Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-19 04:51:19 UTC
Update Date2025-10-07 16:08:00 UTC
Metabolite IDMMDBc0033503
Metabolite Identification
Common NameD-Glycero-D-manno-heptose
DescriptionD-Glycero-D-manno-heptose is a heptose sugar that belongs to the class of carbohydrates. It plays a crucial role in the biosynthesis of lipopolysaccharides, which are essential components of bacterial cell membranes. The enzyme GmhA catalyzes the conversion of sedoheptulose 7-phosphate into D-glycero-D-manno-heptose 7-phosphate, marking the first committed step in its biosynthetic pathway (PMID:38598312 ). Additionally, D-glycero-D-manno-heptose is involved in the assembly of oligosaccharide cores, which include components such as 2-amino-2-deoxy-D-glucose and 3-deoxy-D-manno-oct-2-ulosonic acid (PMID:41003314 ). Its phosphorylated form, D-glycero-D-manno-heptose-1β,7-bisphosphate, is synthesized from D-mannose and is implicated in various biological processes, including bacterial adherence and self-aggregation (PMID:38414338 ). Furthermore, D-glycero-D-manno-heptose is part of the repeating unit in the polysaccharide structure of certain bacterial serotypes (PMID:38386885 ). Recent studies have identified potential inhibitors targeting the enzyme D-glycero-D-manno-heptose-1,7-bisphosphate 7-phosphatase, highlighting its significance in bacterial pathogenicity (PMID:37723879 ).
Structure
SynonymsNot Available
Molecular FormulaC21H42O21
Average Mass630.5456
Monoisotopic Mass630.221858406
IUPAC Name2,3,4,5,6,7-hexahydroxyheptanal; 5-(1,2,3-trihydroxypropyl)oxolane-2,3,4-triol; 6-(1,2-dihydroxyethyl)oxane-2,3,4,5-tetrol
Traditional Name5-(1,2,3-trihydroxypropyl)oxolane-2,3,4-triol; 6-(1,2-dihydroxyethyl)oxane-2,3,4,5-tetrol; D-glycero-D-gulo-heptose
CAS Registry Number1961-73-5
SMILES
OCC(O)C(O)C(O)C(O)C(O)C=O.OCC(O)C(O)C1OC(O)C(O)C1O.OCC(O)C1OC(O)C(O)C(O)C1O
InChI Identifier
InChI=1S/3C7H14O7/c8-1-2(9)6-4(11)3(10)5(12)7(13)14-6;8-1-2(9)3(10)6-4(11)5(12)7(13)14-6;8-1-3(10)5(12)7(14)6(13)4(11)2-9/h2*2-13H,1H2;1,3-7,9-14H,2H2
InChI KeyZHGWJVDOBIMEHL-UHFFFAOYSA-N